In partnership with Workforce Singapore
SINGAPORE: When Eileen Tan co-founded Vintagewknd in 2015, selling upcycled fashion, it was a passion project run from her bedroom.
The 32-year-old and her partner, Eden Tay, have since turned it into a thriving vintage label, with a bricks-and-mortar store in Haji Lane. But success came with strings attached.
“I wish I didn’t have to be the boss,” Tan said. “I suddenly found myself having to wear many hats.”
Years of steering the brand have taken a toll. Burnout has crept in.
She is also battling with the brutal realities of the retail industry, which include rising rents. “The biggest challenge would be (finding) money … to grow the business, expand our team, expand into more spaces,” said Tan, who feels conflicted over her next step.
Also facing a career dilemma is Dan Wong, 42.
He has worked as an illustrator for nearly 15 years, growing A Good Citizen — his art collective — into a steady hub for commercial projects. But the work itself has begun to feel stagnant.
“I’m telling other people’s stories and not my own,” he said. “I don’t know if I intend to be an illustrator for the rest of my life.”
He lectures part-time at the Nanyang Academy of Fine Arts and finds great fulfilment when teaching the younger generation. But he wonders if he can transition to a full-fledged teaching career.
Though at different career stages, Tan and Wong find themselves in the same boat with their self-doubt, not knowing what’s next. So, CNA Insider invited them to Workforce Singapore (WSG) to gain some clarity through career guidance.
Tan tapped the Volunteer Career Advisors (VCA) initiative, pairing up with an industry mentor for insights into both self-growth and business growth; and Wong enrolled in Polaris, a personalised career coaching programme, which helped him map out his career path.
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The VCA initiative helps Singaporeans and permanent residents take charge of their careers, with peer support and industry insights from professionals across various sectors.
For Tan, consulting a career adviser is not only about growth but also about clarity. “I want someone with experience, who can guide me and help me figure out the best path forward," she said.
She found a “good match” in Nicholas Singh, a branding consultant with over 30 years of experience. After reviewing her résumé, he did not hold back in their session.
“Right now, your business has reached such a stage (that) you think, if you’re not involved, it’ll be dead. … You are your biggest limitation,” he said, referring to her tendency to struggle with delegation.
He pointed out a common blind spot for high achievers: perfectionism.
“We hold ourselves to such high standards … (that) it’ll deplete us,” he said. “It’ll affect our relationships with people we work with, our family members and such.”
But it was not all tough love; he also recognised her strengths. With her expertise in sustainable business, branding, marketing and leadership, she was well placed for opportunities “outside the shop”.
These included advisory board positions and developing coaching frameworks with her know-how. Instead of simply running a business, she could start shaping the industry — something Tan had never considered.
“I didn’t know if I was qualified, even though I’d been doing it for quite (some time),” she said.
To help her manage stress and avoid burnout, Singh introduced her to cognitive behavioural therapy techniques. He also offered to overhaul her LinkedIn bio, rewriting it to showcase her experiences and passions.
“Being an entrepreneur is an extremely lonely journey,” he said. Therefore, having a career coach or “someone else to be accountable to”, besides oneself, could make a difference.
Wong, meanwhile, took Polaris, a career guidance programme offered by WSG.
He and career coach Asher Liew — who had three sessions together — worked at the outset to identify the root cause of his problem.
And it did not take long before Wong realised that his feeling of exhaustion was not a recent issue: It had plagued him for much of his career, stemming either from overwork or a lack of passion for his job.
“My father serviced military aircraft and was a workaholic,” Wong shared. “Maybe that’s why I internalised the idea that work and career should always come first.”
For Liew, the key is not for clients to recount every detail of their lives but to achieve meaningful introspection.
In his first session with Wong, he focused on setting intentions and helping Wong pinpoint what truly motivated him.
To do this, Liew introduced a card-sorting exercise that helped distinguish between Wong’s "motivated skills" (things he enjoyed doing and was good at) and “burnout skills” (tasks that he was competent in but were mentally draining).
The second session focused on understanding what energised him via a profiling tool. The results were unexpected. “It’s very strange; it classified me as not very imaginative,” Wong said. “But in my head, I’m super imaginative.”
In response, Liew suggested: “His pragmatic side might compromise his imagination when it comes to dealing with creative items.”
It was this insight that prompted Wong to rethink his career path, especially having discovered that people development, in terms of mentoring and coaching others, was a skill he found invigorating.
The final session explored the skills he would need to transition to teaching. While he was qualified to teach diploma courses, he lacked the master’s degree required for university-level instruction.
“The cost of doing a master’s in Singapore isn’t cheap,” remarked Wong, who thought of “having discussions with people who are close to me to see whether it’s feasible”.
Ultimately, he was seeking not only a career pivot but also work that was sustainable, fulfilling and would enable him to build a life he could be happy with, even if it meant adjusting some long-term goals.
Volunteer Career Advisors initiative
Polaris
With the career guidance Tan received, she has made some adjustments already. In the weeks after first connecting with Singh, she has put his advice into practice, focusing on better delegation and actively listening to her team.
“I’ve definitely seen quite a few changes,” Tay observed. “Eileen is a lot more communicative about (her) ideas … and open to the other party’s views as well.”
Tan has also started developing an online portfolio to position herself as a thought leader in sustainability. “I (now) have … better direction, (relying) on someone with a lot of experience giving me advice,” she said.
Wong, too, walked away with a renewed sense of optimism. Initially, he was apprehensive that career coaches would not quite get what he was going through, but that was not the case at all.
“My time with Asher has been incredibly productive and insightful,” affirmed Wong, who feels a weight off his shoulders.
Although the sessions did not provide quick and easy solutions, he soon realised that their true worth lay in understanding himself and finding his own way forward.
“When it comes to career planning, … it’s important for you to take (the) initiative,” advised Liew, who will be following up on Wong’s career development plan after a few weeks.
For mid-career individuals like Tan and Wong, there are also career tools such as CareersFinder and CareersCompass — accessible via the job portal MyCareersFuture — which offer customised upskilling and career development insights.
Along with these programmes, WSG offers a slew of resources to help individuals navigate their career journeys, no matter the stage.
This includes Career GRIT, an easy-to-use platform with job opportunities, career advice and workshops. Career fairs, workshops and job placement support are also available for those looking to explore new paths.
The concept behind these resources is to empower workers to make more informed career decisions to achieve their aspirations and develop resilient, fulfilling careers.
“You’re solely in charge of your own career health,” Liew said. “Help is definitely available out there, and I sincerely hope that more people are seeing the importance of taking care of themselves in terms of their career.”
Connect with a VCA via this link. Or for more information about Polaris, click here.
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